Chloroform → (S)-t-Butyl 2-(3-((3,4-dimethoxyphenoxy)methyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Chloroform	HCID 6212	—
Reactant	1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-	HCID 85083	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	2-(3,4-Dimethoxyphenoxy)-N'-hydroxyacetoimidamide	HCID 86706761	—
Solvent	Water	HCID 962	—
Product	(S)-t-Butyl 2-(3-((3,4-dimethoxyphenoxy)methyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate	HCID 86706762	10.6%

Reaction Steps

To a CHCl3 (20 ml) solution of the compound (1.0 g) obtained in Example 12-(1) and (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.0 g), WSC.HCl (1.0 g) was added and the mixture was stirred at room temperature for 4 hours. Water was added, followed by extraction with CHCl3. After distilling off the solvent under reduced pressure, the residue was dissolved in toluene (20 ml), followed by refluxing for 2 hours. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (190 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181229B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-c6ddbeae3619443382fac0b2f0710606
Source note	uspto-grants-2015_11